Written by Capt. Chris Dollar
The Rolling Stones had it right. While you can’t always get what you want, if you try sometime, you get what you need. That’s why—in the clutches of a global pandemic—the Chesapeake is just what we need: an awesome place for outdoor pursuits. My pursuits tend to be literal, chasing after fish or game, but whether you’re looking for a great place to paddle or chasing the perfect sunset, you can find it on the Bay.
Catching a spunky rockfish on a top water fly ranks high on my list of best things about the Chesapeake, but it’s just one experience on a long list that includes stalking speckled trout and puppy drum in the skinny waters surrounding our marsh islands, wrestling with brutish cobia, outwitting houndfish, playing chess with freshwater trout, or seeking out the less glamorous Chesapeake species like spadefish, blue cats or snakeheads. Crabbing is just pure fun.
Fish brim with wild vitality, and by extension allow me to do the same. Coming tight to a fish—big or small—brings an adrenaline rush, which is calibrated to the particulars of that fish and the circumstances of how you hook it. When you reach a certain point in life, the metaphysical “last cast” helps keep the endless churn of time at arm’s length.
Other favorites include spying a flock of ducks cupped up in majestic descent, a scene nothing short of inspirational. A Chesapeake marsh is a magical place, and for me it holds a special solitary beauty in winter. Here you’ll find gadwall, teal, black ducks, and widgeon. Open rivers and the Bay are the territory of diving ducks like scaup, canvasbacks and redheads, fearless in the face of howling winds and biting whitecaps.
Few images say Chesapeake like a brace of Canada geese gliding in near perfect symmetry, wing-and-wing, on their final approach with their pillowy white undercarriage laid bare, black webbed feet dangling like marionettes mere feet above our plastic foils.
Or, through a veil of fog distorting dawn’s half-light, catching fleeting glimpses of a mature Tom (turkey), its Chestnut-brown fan barely visible, stealthily crossing the woods.
No doubt hunting and fishing offer lasting family memories and camaraderie, as well as exquisite fried chicken and egg-and-scrapple sandwiches. For me it goes deeper. Being outdoors immerses me in the natural cycle of life, warding off a technical world consumed with “likes,” “views,” and “clicks.” No better place to do it than here on Chesapeake Bay.
Most Charming Chesapeake Town
Maryland: Solomons
Whether you arrive by boat or car, Solomons offers attractions ranging from the Calvert Marine Museum (see “Best Maritime Museum”) to fossil-hunting at Calvert Cliffs to the Annmarie Gardens and Sculpture Park, along with a ton of restaurants, hotels, and B&Bs to make a weekend of it.
Virginia: Yorktown
History is at the center of the Yorktown experience, as befits the site of the last battle of the Revolutionary War, but they’ve updated the place a bit since then, with fine dining options, shopping, and events like art shows and outdoor concerts.
Best Maritime Museum
Maryland: Calvert Marine Museum, Solomons
More than a maritime museum, Calvert covers everything from otters to oyster shuckers, with stops for traditional small craft, prehistoric fossils, and wood carving.
Virginia: Mariners’ Museum & Park, Newport News
From the Age of Exploration to the latest America’s Cup advances, the Mariners’ Museum packs in basically everything you want to know about boats, including construction from carbon fiber to buffalo hide, as well as art, models, and artifacts galore.
Best Community Museum
Maryland: Harriet Tubman Museum and Education Center, Cambridge
The site of Cambridge’s epic Harriet Tubman mural, this volunteer-run museum was started in the 1980s to honor one of Maryland’s greatest.
Virginia: Watermen’s Museum, Yorktown
It’s dedicated to the watermen, obviously, but this little museum has big ideas, emphasizing environmental stewardship, native and colonial history, and ongoing research into the maritime legacy of the Bay.
Best Public Beach
Maryland: Flag Ponds Nature Park, Lusby
A short hike through the woods reveals a natural sandy beach, perfect for swimming, playing, and searching for fossils and shark teeth.
Virginia: Yorktown Beach, Yorktown
A two-acre beach near Riverwalk Landing and the rest of Yorktown’s attractions, Yorktown Beach is open to sunbathing, swimming, and general beach shenanigans, and includes an accessible beach path for wheelchairs.
Best Couples’ Escape
Maryland: Cove Point Lighthouse Keeper’s House, Lusby
Missed your chance to marry a lighthouse keeper? You can still pretend. This renovated duplex owned by the Calvert Marine Museum is available for three-, four- and seven-day rentals of one or both sides of the duplex.
Virginia: Hornsby House Inn, Yorktown
A family home built in 1933, Hornsby House was opened as a bed and breakfast in 2011 on Yorktown’s Main Street. It’s walking distance to restaurants and shops, and a short drive to the area’s many historic attractions.
Best Family Getaway
Maryland: Calvert Marine Museum, Solomons
In addition to the skate and ray touch tank and the paleontology prep lab, there are usually activities scheduled at the museum for “sea squirts” (18 months to three years) and “little minnows” (three to five).
Virginia: Colonial National Historical Park, Yorktown
Turn your kid into a history buff by traveling the 23-mile Colonial Parkway from Yorktown Battlefield (“Look kids, cannons!”) to Historic Jamestown (“Look kids, glassblowers!”) and everything in between.
Best Lighted Boat Parade
Maryland: Solomons
Held in conjunction with the Solomons Christmas Walk, this boat parade caps a week-long celebration of all things lighted. Walk around and see the houses and the tree-lighting, then hit the docks for some nautical holiday cheer.
Virginia: Yorktown
It remains to be seen what this year’s parade will bring, but hopefully it will involve the usual beach bonfire and watching the parade of sail and powerboats compete for best in show.
Best Holiday Display
Maryland: Rock Hall
Nothing says Eastern Shore like their community crab basket Christmas tree, made with donated, hand-painted baskets and topped with a glowing red crustacean.
Virginia: Old Town Alexandria
This waterfront town of brick streets and 18th-century rowhouses is never prettier than when its dressed for the holidays, with twinkling lights and greenery, strolling carolers and hand bells choirs, and an air of timeless excitement. It’s straight out of Dickens, minus the Scrooge.
Best Place to Camp
Maryland: Assateague State Park
This just might be the prettiest beach in Maryland, with RV campsites, tent-only sites convenient to a parking lot, and back-country, walk-in sites. Oceanfront tent sites 101 to 104 are located at the southern end for maximum privacy.
Virginia: Bethpage Camp-Resort, Urbanna
Call it a camp for people who don’t like tents; instead, you’ll find plentiful RV hookups and private rental cottages with full kitchens and covered decks. Amenities include a boat ramp, lake beach, water park, cow-themed mini-golf, and activities for all ages.
Best Scenic Drive
Maryland: Harriet Tubman Byway
This 125-mile, self-guided route winds through Eastern Shore, bringing the abolitionist heroine to life via evocative stops like the circa-1830 Bucktown Village Store, where she took her first risk to help an enslaved man.
Virginia: Colonial Parkway
This 23-mile scenic highway connects the historic triangle of Yorktown, Jamestown and Williamsburg. Stop along the way for history lessons via interpretive markers, or just cruise and enjoy the protected landscape, managed by the National Park Service.
Best Bicycling Excursion
Maryland: C&D Canal Trail, Chesapeake City
Parallel the ship traffic on the north side of the storied canal from Delaware Bay to the Maryland State line, then continue along to Chesapeake City on this 14-mile paved path.
Virginia: James River Park System, Richmond
Explore 22 miles of riverside biking and walking trails that meander through this capital city, or hone your off-road technique at the purpose-built skills park, tucked under the Lee Bridge.
Best Place for Hiking
Maryland: Calvert Cliffs State Park
This stretch of cliffs in southern Maryland is estimated to be up to 20 million years old, with the prehistoric fossils to prove it, so keep your eyes peeled as you roam the 13 miles of trails.
Virginia: Dismal Swamp Canal Trail
The Dismal Swamp Canal is a boating rite of passage, and the oldest continuously operating man-made canal in the U.S. Bike (or hike or ride) alongside it on this 8.3-mile asphalt trail, repurposed from a former section of Route 17.
Best Historical Site
Maryland: Handsell House, Vienna
Sections of this handsome brick Georgian predate the Revolution. While the house itself is undergoing restoration, outside displays share details on the Native and African American people who lived, worked and traded here.
Virginia: Historic Williamsburg
An open-air museum like no other, this 301-acre testament to our earliest days always has something new to discover, no matter how many times you’ve been there.
Best Birdwatching
Maryland: Blackwater Wildlife Refuge
This refuge spans more than 28,000 acres of marsh and lowland forest, making it one of the premier stops on the Atlantic Flyway for tundra swans, Canada geese and more than 20 species of duck.
Virginia: Chincoteague National Wildlife Refuge
The resident horses get the attention, but birders know it’s tops in the state for birds too; over 350 species have been recorded here, from egrets and ibis to the rarer Sabine’s Gull.
Best Golf Course
Maryland: Chesapeake Bay Golf Club, Rising Sun
This 18-hole, semi-private course at the top of the Bay gets raves for well-maintained fairways, rolling greens and a few doglegs to keep it interesting.
Virginia: Cypress Creek, Smithfield
This par-71, 7,169-yard course is the gem of the Tidewater area, managed under a trio of new local owners in July 2019.
Best Place to Find Sharks Teeth
First place: Westmoreland Cliffs, VA
Here’s another fun activity for the family. Kids love it because they don’t have as far to bend over as we do, and their eyes are better. Many of the Bay’s cliffs are best viewed from a boat, but there are a few places where you can stop to scan the shores for relics of the Miocene and all those other eras when all this was part of the sea. Westmoreland State Park is a good example; it’s a beautiful park, with a nice, sandy beach for fossil hunting and a good launch site for paddlecraft and trailer boats. You can camp here or rent a cabin.
Second place: Calvert Cliffs, MD
While the Virginia side of the Potomac has Westmoreland, Nomini and Stratford cliffs, the Maryland Western Shore of the Bay has the 24-mile long Calvert Cliffs, which stretch north from the Patuxent River. On a calm day, you can anchor off the cliffs and dinghy ashore to hunt sharks’ teeth. Alternatively, you can approach the cliff beaches through Calvert Cliffs State Park.
Third place: Calvert Marine Museum, Solomons Island, MD
If the first two options are too, well, messy, then take the boat or land yacht to Solomons Island to visit the excellent Calvert Marine Museum. The museum has a very large collection of fossils and a whiz-bang Paleontology Gallery. They will also help you identify the items you’ve found at Westmoreland or Calvert Cliffs.
Best Unconventional Historical Site
First place: Structural glass, Menokin, VA
Menokin was built in 1769 as a wedding gift for Revolutionary hero Francis Lighthorse Lee and Rebecca Tayloe. The Lees and the Tayloes were a union of soap-opera proportions. Two hundred years later, however, the home was in near ruins and workers removed two thousand pieces of architectural detail to be stored until the home could one day be restored. Another half-century later, and what remains of Menokin stands in an empty field, sheltered by a great canopy. Now plans are in place to put the house back together—but with a difference. Instead of new wood siding and shingled roofs, the missing pieces will be replaced with structural glass, so that building’s inner structure will be visible to visitors. It’s going to be a revolutionary restoration. Menokin is located on the Northern Neck of Virginia on Cats Point Creek, off the Rappahannock River. This creek, by the way, is the perfect place to paddle back through time. No motors allowed.
Second place: Ghost houses, St. Mary’s City, MD
St. Mary’s City was, of course, the founding settlement and first capital of the Colony of Maryland. And, as I’m sure you know, it was virtually abandoned after the capital was moved to Annapolis. Since then, some of its major buildings have been reconstructed, and a lot archeological work has been done. It’s a great place to visit and one you can get to easily by boat, but to me the most memorable thing about it, the image that lingers in my mind, are its ghost frames: structural outlines of lumber that mark the location and shape of buildings that have long since disappeared. Visit by car and launch a kayak into the St. Marys River. Or better yet, cruise up the St. Marys on your boat and anchor off the beach in Horseshoe Bend.
Best Cruise of Unglamorous Lighthouses
First place: The Potomac River
Point Lookout Lighthouse, MD
Let’s begin with Point Lookout Lighthouse, which marks the shoal off the northern shore of the Potomac River. You’ll have to look hard to find this lighthouse, because it sits, not out on the shoal—there are other markers that take care of that job—but on Port Lookout itself. Look for a two-story farmhouse with a light on top. That’s it. The lighthouse was built in 1830, endured a clumsy keeper who broke most of the lights, was the site of rather gruesome doings during the Civil War, and since its decommissioning, has been a favorite site for paranormal investigation. The lighthouse is part of Point Lookout State Park, where you can launch a trailer boat or paddlecraft if you’d rather come at it that way.
Fort Washington Light, MD
The first Fort Washington Light was authorized in the early 1800s by U.S. Secretary of War Jefferson Davis (yes, that one). It went through several iterations until 1901, when it ended up as a light placed temporarily on top of a fog bell tower. It’s still a light placed temporarily on top of a fog bell tower. You can’t miss it because you’ll never see another navigation marker
like it.
Jones Point Lighthouse, VA
Finally, we come to the littlest lighthouse of all: Jones Point, a one-story house with a lantern on top that was built in 1855. If you visit by land, look on its seawall, where you’ll find the south cornerstone of the original survey for the District of Columbia. One of its keepers, Benjamin Greenwood, lived in this tiny, four-room house with his wife and 11 of their 14 children. (Did the others sleep outside?) Now it’s part of Jones Point Park and sits nearly under the Woodrow Wilson Bridge.
